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US5849938A - Separation of methanol and propylene oxide from a reaction mixture - Google Patents

Separation of methanol and propylene oxide from a reaction mixture Download PDF

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Publication number
US5849938A
US5849938A US08/926,420 US92642097A US5849938A US 5849938 A US5849938 A US 5849938A US 92642097 A US92642097 A US 92642097A US 5849938 A US5849938 A US 5849938A
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United States
Prior art keywords
methanol
extractive distillation
distillation zone
reaction product
propylene oxide
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Expired - Lifetime
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US08/926,420
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English (en)
Inventor
Michael A. Rueter
John C. Jubin, Jr.
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Lyondell Chemical Technology LP
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Arco Chemical Technology LP
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Application filed by Arco Chemical Technology LP filed Critical Arco Chemical Technology LP
Priority to US08/926,420 priority Critical patent/US5849938A/en
Assigned to ARCO CHEMICAL TECHNOLOGY, L.P. reassignment ARCO CHEMICAL TECHNOLOGY, L.P. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JUBIN, JOHN C., JR., RUETER, MICHAEL A.
Priority to JP2000508678A priority patent/JP2001514258A/ja
Priority to KR1020007002086A priority patent/KR20010023443A/ko
Priority to PCT/EP1998/005470 priority patent/WO1999011639A1/en
Priority to CN98808688A priority patent/CN1268946A/zh
Priority to EP98951325A priority patent/EP1009746B1/en
Priority to CA002301060A priority patent/CA2301060A1/en
Priority to BR9811423-9A priority patent/BR9811423A/pt
Priority to ES98951325T priority patent/ES2175803T3/es
Priority to AU97397/98A priority patent/AU9739798A/en
Priority to DE69804638T priority patent/DE69804638T2/de
Publication of US5849938A publication Critical patent/US5849938A/en
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Assigned to CITIBANK, N.A., AS ADMINISTRATIVE AGENT reassignment CITIBANK, N.A., AS ADMINISTRATIVE AGENT SECURITY AGREEMENT Assignors: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Assigned to WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT reassignment WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT SECURITY AGREEMENT Assignors: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Assigned to LYONDELL CHEMICAL TECHNOLOGY, L.P. reassignment LYONDELL CHEMICAL TECHNOLOGY, L.P. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: DEUTSCHE BANK TRUST COMPANY AMERICAS
Assigned to LYONDELL CHEMICAL TECHNOLOGY, L.P. reassignment LYONDELL CHEMICAL TECHNOLOGY, L.P. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CITIBANK, N.A.
Assigned to LYONDELL CHEMICAL TECHNOLOGY, L.P. reassignment LYONDELL CHEMICAL TECHNOLOGY, L.P. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: WELLS FARGO BANK, NATIONAL ASSOCIATION
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/32—Separation; Purification
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
    • B01D3/40—Extractive distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms

Definitions

  • This invention provides a method of recovering propylene oxide in purified form from an epoxidation reaction mixture which additionally contains methanol.
  • Such mixtures may be formed by epoxidizing propylene with hydrogen peroxide using a titanium-containing zeolite as a catalyst and methanol as a reaction solvent.
  • a hydroxy group-containing polar solvent such as water or propylene glycol is used as an extractive solvent in a distillation column so as to enhance the difference in volatility between propylene oxide and methanol, thereby permitting propylene oxide to be withdrawn as an overhead stream from the column.
  • the extractive distillation may also be operated to reduce the level of other undesirable impurities such as water and acetaldehyde in the propylene oxide.
  • the crude reaction product thereby obtained typically contains only about 2 to 10 weight percent propylene oxide with the balance being predominantly methanol.
  • propylene oxide and methanol normally have similar boiling points and thus can be difficult to separate quantitatively, especially where methanol is present in large excess. Minor quantities of certain by-products such as acetaldehyde are inevitably formed during epoxidation and subsequent processing. Since a satisfactory propylene oxide for commercial purposes should contain less than 100 ppm, and preferably less than 20 ppm, acetaldehyde, the development of methods for reducing the level of acetaldehyde by-product in such reaction mixtures is necessary.
  • epoxidation processes of this type form water as a co-product, with the water being derived from the hydrogen peroxide oxidant.
  • water may also be present in the feed to the reactor. While epoxidation processes catalyzed by titanium-containing zeolites are remarkably tolerant of water, it will be necessary for most commercial purposes to obtain propylene oxide in substantially anhydrous form. Thus, it is apparent that there is a need to develop purification methods capable of efficiently removing methanol, water and acetaldehyde simultaneously from a crude epoxidation reaction product when propylene oxide is present at a relatively low concentration.
  • a crude epoxidation reaction product comprised of propylene oxide and methanol may be purified by the following process.
  • the crude epoxidation reaction product is introduced into an intermediate section of an extractive distillation zone, while also introducing a polar solvent having a hydroxy functionality and a boiling point higher than that of methanol into an upper section of the extractive distillation zone.
  • Propylene oxide is distilled overhead from said extractive distillation zone, with a bottoms stream comprised of methanol and the polar solvent withdrawn from a lower section.
  • the process can be operated such that the water and at least a portion of the acetaldehyde present in the crude epoxidation reaction product are extracted into the polar solvent and removed in the bottoms stream.
  • FIG. 1 to be explained in more detail hereafter, illustrates in schematic form an embodiment of the invention.
  • the crude epoxidation reaction product treated in accordance with the process of this invention is typically obtained by epoxidizing propylene with hydrogen peroxide or an equivalent thereof in a reaction medium where methanol is used as a solvent.
  • Any unreacted propylene which may be present may be first largely or entirely removed by subjecting the crude epoxidation reaction product to an initial separation or fractionation using conventional distillation methods.
  • the propylene may be removed overhead using a flash drum or the like.
  • the epoxidation catalyst which may be, for example, a titanium-containing zeolite such as titanium silicalite, is preferably also separated by filtration or other such means from the crude epoxidation reaction product prior to processing in accordance with the present invention.
  • the crude epoxidation reaction product typically will have a composition comprised of the following components, in percent by weight:
  • the propylene glycol concentration range shown above includes the embodiment of the invention wherein propylene glycol is utilized as the polar solvent in the extractive distillation step and the propylene glycol recovered in the bottoms stream is incompletely separated from the methanol prior to recycling the methanol for use in epoxidation.
  • the amount of propylene glycol actually generated as a by-product of epoxidation will represent less than 1 weight % of the crude epoxidation reaction product. If a glycol other than propylene glycol or another heavy component is utilized as the polar solvent in the aforedescribed embodiment, then the concentration of said polar solvent in the crude epoxidation reaction product will be higher than the range shown in the above table.
  • the extractive distillation is suitably carried out in any convenient distillation column or tower appropriate for the distillation of propylene oxide and methanol.
  • the extractive distillation zone should contain at least 10 theoretical plates and ordinarily will contain 20 to 60 theoretical plates. The maximum number of theoretical plates is limited only by economic considerations. A single distillation column or tower is usually preferred for economic reasons, but the use of multiple distillation columns to accomplish the same result is not excluded.
  • the polar solvent to be supplied to the extractive distillation zone is a compound containing one or more hydroxy (--OH) functional groups and having a boiling point higher than that of methanol.
  • suitable classes of polar solvents include, but are not limited to, glycols and glycol ethers. Glycols containing from 2 to 6 carbon atoms and oligomers thereof (e.g., dimers, trimers and tetramers) are generally suitable for use.
  • Illustrative glycols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,4-butanediol, 2-methyl-1,3-propanediol, neopentyl glycol and the like and oligomers thereof.
  • Illustrative glycol ethers include the C 1 -C 6 alkyl ethers of propylene glycol, ethylene glycol and oligomers thereof such as di- and tripropylene glycol and di- and triethylene glycol. Mixtures of polar solvents (e.g., aqueous propylene glycol) could also be utilized.
  • the amount of polar solvent supplied to the extractive distillation zone should be sufficient to achieve the desired degree of separation of methanol and other impurities such as acetaldehyde and water from the propylene oxide. This amount will vary, of course, depending upon a number of factors, including the identity of the polar solvent, but generally will be at least about 5%, based on the weight of the crude epoxidation reaction product.
  • the polar solvent is fed to the extractive distillation zone at a rate (on a weight basis) which is from 5 to 35 percent of the feed rate of the crude epoxidation reaction product.
  • the point at which the crude epoxidation reaction product is introduced is an intermediate section of the extractive distillation zone, preferably from about 40% to 70% of the distance, in terms of theoretical plates, from the bottom to the top of the extractive distillation zone.
  • a suitable reflux/distillate ratio is important in achieving optimum results and generally will be in the range of from 5:1 to 15:1.
  • the pressure under which the extractive distillation is operated is suitably around atmospheric pressure, e.g., from about 8 up to about 50 psia.
  • the bottoms (reboiler) temperature will, of course, vary with the pressure but will typically be within the range of 90° C. to 120° C.
  • the extractive distillation conditions are selected so as to provide an overhead stream comprised predominately of propylene oxide.
  • at least 95 weight % (more preferably at least 98 weight %) of the overhead stream is propylene oxide.
  • the overhead stream will preferably contain less than 0.5 weight percent water (more preferably less than 0.05 weight percent water) and less than 1 weight percent methanol (more preferably, less than 0.2 weight percent methanol).
  • the bottoms stream withdrawn from the extractive distillation will contain all or essentially all (i.e., 99+%) of the polar solvent (including any water present in the crude epoxidation reaction product) and a preponderance of the methanol (e.g., 99+%) originally present in the crude epoxidation reaction product.
  • varying amounts of the acetaldehyde will be removed in the bottoms stream (e.g., 50 to 98%) while still achieving the desired separation of propylene oxide from methanol. For example, adjustments in reflux ratio, number of theoretical trays, overhead cut point and extractive solvent flow will change the acetaldehyde distribution.
  • fractionator 6 may be significantly reduced in size (and thus cost) as compared to the fractionator which would be required if the reaction mixture was directly subjected to fractional distillation rather than an initial extractive distillation.
  • a further advantage is that fractionation of the acetaldehyde and propylene oxide is accomplished much more easily in the absence of methanol; the present process thus facilitates complete acetaldehyde removal by providing an overhead stream which is essentially free of methanol.
  • the methanol in the bottoms stream may advantageously be recycled for use as the reaction solvent in an olefin epoxidation process, preferably after at least partial separation from the polar solvent by distillative means or the like.
  • the separated polar solvent may likewise be recycled for further use in the present extractive distillation process.
  • the bottoms stream may be fed through line 4 to an intermediate section of fractionator 9 and subjected to fractional distillation. Methanol and other components of the bottoms stream which are more volatile than the polar solvent are removed overhead from fractionator 9 via line 10.
  • the polar solvent recovered in the bottoms stream is returned to extractive distillation zone 2 through line 3.
  • the extractive distillation process described in application Ser. No. 08/911,972, filed Aug. 15, 1997 (Attorney's Docket No. 01-2467A) may be utilized to remove at least a portion of any residual acetaldehyde from the methanol prior to its reuse in epoxidation if so desired.
  • the crude epoxidation reaction product is fed to an extractive distillation tower containing 50 theoretical stages (including reboiler), the feed point being 19 stages from the top of the tower.
  • Propylene glycol is fed to the 4th stage from the top of the tower at a flow rate which is 13.4% of the crude epoxidation reaction product flow rate on a weight basis.
  • a purified propylene oxide product is taken as an overhead distillate.
  • the propylene glycol extractive solvent is withdrawn from the bottom stage (reboiler), together with all, or nearly all, of the methanol and water as well as other relatively heavy components.
  • the tower is operated at a reflux ratio (reflux-to-distillate) of 9.
  • the pressure in the column condenser is set at 30 psia and the column operated with a pressure drop of 0.2 psi per tray, resulting in a bottom pressure of about 40 psia.
  • the bottoms (reboiler) temperature is 104° C. and the top (condenser) temperature is 51° C.
  • the crude epoxidation reaction product is fed to an extractive distillation tower containing 25 theoretical stages (including reboiler), the feed point being 13 stages from the top of the tower.
  • Propylene glycol is fed to the third stage from the top at a flow rate which is 28% of the flow rate of the crude epoxidation reaction product feed on a weight basis.
  • a purified propylene oxide product is taken as an overhead distillate.
  • the propylene glycol extractive solvent is withdrawn from the bottom stage (reboiler), together with all or nearly all of the water and methanol as well as other components.
  • the tower is operated at a reflux ratio (reflux-to-distillate) of 9.
  • the pressure in the column condenser is set at 30 psia and the column operated with a pressure drop of 0.2 psi per tray such that the bottom pressure is approximately 37 psia.
  • a bottoms (reboiler) temperature of 105° C.
  • a top (condenser) temperature of 51° C.
  • compositions of the product streams are as follows:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Epoxy Compounds (AREA)
US08/926,420 1997-09-02 1997-09-02 Separation of methanol and propylene oxide from a reaction mixture Expired - Lifetime US5849938A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US08/926,420 US5849938A (en) 1997-09-02 1997-09-02 Separation of methanol and propylene oxide from a reaction mixture
KR1020007002086A KR20010023443A (ko) 1997-09-02 1998-08-28 반응 혼합물로부터 메탄올 및 프로필렌 옥시드의 분리방법
DE69804638T DE69804638T2 (de) 1997-09-02 1998-08-28 Trennung von methanol und propylenoxid aus einem reaktiosgemisch
JP2000508678A JP2001514258A (ja) 1997-09-02 1998-08-28 反応混合物からのメタノールとプロピレンオキシドの分離
PCT/EP1998/005470 WO1999011639A1 (en) 1997-09-02 1998-08-28 Separation of methanol and propylene oxide from a reaction mixture
CN98808688A CN1268946A (zh) 1997-09-02 1998-08-28 从反应混合物中分离甲醇和氧化丙烯的方法
EP98951325A EP1009746B1 (en) 1997-09-02 1998-08-28 Separation of methanol and propylene oxide from a reaction mixture
CA002301060A CA2301060A1 (en) 1997-09-02 1998-08-28 Separation of methanol and propylene oxide from a reaction mixture
BR9811423-9A BR9811423A (pt) 1997-09-02 1998-08-28 Separação de metanol e óxido de propileno a partir de uma mistura de reação
ES98951325T ES2175803T3 (es) 1997-09-02 1998-08-28 Separacion de metanol y oxido de propileno de una mezcla de reaccion.
AU97397/98A AU9739798A (en) 1997-09-02 1998-08-28 Separation of methanol and propylene oxide from a reaction mixture

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/926,420 US5849938A (en) 1997-09-02 1997-09-02 Separation of methanol and propylene oxide from a reaction mixture

Publications (1)

Publication Number Publication Date
US5849938A true US5849938A (en) 1998-12-15

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US08/926,420 Expired - Lifetime US5849938A (en) 1997-09-02 1997-09-02 Separation of methanol and propylene oxide from a reaction mixture

Country Status (11)

Country Link
US (1) US5849938A (zh)
EP (1) EP1009746B1 (zh)
JP (1) JP2001514258A (zh)
KR (1) KR20010023443A (zh)
CN (1) CN1268946A (zh)
AU (1) AU9739798A (zh)
BR (1) BR9811423A (zh)
CA (1) CA2301060A1 (zh)
DE (1) DE69804638T2 (zh)
ES (1) ES2175803T3 (zh)
WO (1) WO1999011639A1 (zh)

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002088103A1 (fr) * 2001-04-27 2002-11-07 Sumitomo Chemical Company, Limited Procede de fabrication d'oxyde de propylene
US20020189450A1 (en) * 2001-06-18 2002-12-19 Willi Hofen Process for the recovery of combustible components of a gas stream
US6500311B1 (en) * 2001-09-21 2002-12-31 Arco Chemical Technology, L.P. Propylene oxide purification
US6596881B2 (en) 2001-06-13 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6596883B2 (en) 2001-08-23 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6600055B2 (en) 2001-06-13 2003-07-29 Degussa Ag Process for the epoxidation of olefins
US6608219B2 (en) 2001-06-13 2003-08-19 Degussa Ag Process for the epoxidation of olefins
US6610865B2 (en) 2001-08-15 2003-08-26 Degussa Ag Process for the epoxidation of olefins
US6617465B2 (en) 2001-01-08 2003-09-09 Degussa Ag Process for the epoxidation of olefins
US6624319B2 (en) 2000-02-07 2003-09-23 Degussa Ag Process for the epoxidation of olefins
US6646141B2 (en) 2000-02-07 2003-11-11 Degussa Ag Process for the epoxidation of olefins
US6670492B2 (en) 2000-02-07 2003-12-30 Degussa Ag Process for the expoxidation of olefins
US20040000473A1 (en) * 2002-06-20 2004-01-01 Willi Hofen Process of separating 1-methoxy-2-propanol and 2-methoxy-1-propanol from aqueous compositions
US20040006239A1 (en) * 2002-05-02 2004-01-08 Thomas Haas Process for the epoxidation of olefins
US6720436B2 (en) 2002-03-18 2004-04-13 Degussa Ag Process for the epoxidation of olefins
US20040101462A1 (en) * 2002-09-30 2004-05-27 Thomas Haas Aqueous hydrogen peroxide solutions and method of making same
US20040110970A1 (en) * 2002-11-26 2004-06-10 Thomas Haas Process for the epoxidation of olefins
US20040127730A1 (en) * 2002-09-30 2004-07-01 Thomas Haas Process for the epoxidation of olefins
US20060006054A1 (en) * 2004-07-07 2006-01-12 Basf Aktiengesellshaft Separation of propylene oxide from a mixture comprising propylene oxide and methanol
US20060009648A1 (en) * 2004-07-07 2006-01-12 Basf Aktiengesellschaft Separation of propylene oxide from a mixture comprising propylene oxide and methanol
US20060113180A1 (en) * 2003-03-18 2006-06-01 Renate Patrascu Purification of propylene oxide resulting from epoxidation of propylene with hydrogen peroxide
US7105687B1 (en) * 2005-12-22 2006-09-12 Lyondell Chemical Technology, L.P. Propylene oxide purification and recovery
WO2010024839A1 (en) * 2008-08-29 2010-03-04 Lyondell Chemical Technology, L.P. Propylene oxide process
US20130109872A1 (en) * 2010-07-14 2013-05-02 Dow Global Technologies, Llc Process and assembly for producing alkylene oxides and glycol ethers
CN103172596A (zh) * 2011-12-22 2013-06-26 中国石油化工股份有限公司 一种环氧丙烷精制方法
CN103172595A (zh) * 2011-12-22 2013-06-26 中国石油化工股份有限公司 一种从直接环氧化反应产物中提纯环氧丙烷的方法
US8981133B2 (en) 2011-06-07 2015-03-17 Lyondell Chemical Technology, L.P. Alkylene oxide separation systems, methods, and apparatuses
US9278945B2 (en) 2013-12-06 2016-03-08 Shell Oil Company Relating to propylene oxide purification
CN113801076A (zh) * 2020-06-16 2021-12-17 江苏怡达化学股份有限公司 环氧丙烷精馏工艺

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4078482B2 (ja) * 2002-02-15 2008-04-23 住友化学株式会社 プロピレンオキサイドの精製方法
EP1424332A1 (en) * 2002-11-26 2004-06-02 Degussa AG Process for the purification of crude propene oxide
KR100846435B1 (ko) * 2006-12-22 2008-07-16 한화석유화학 주식회사 옥시란 화합물의 제조 방법
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AU9739798A (en) 1999-03-22
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WO1999011639A1 (en) 1999-03-11
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CA2301060A1 (en) 1999-03-11
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